Flexible Entry into 3-Arylpent-2-enedioic Acids via Heck-Matsuda Arylation of Dimethyl Glutaconate with Arenediazonium Tosylates

Synthesis 2019
Dmitry Dar`in, Grigory Kantin, Raivis Žalubovskis, Mikhail Krasavin

For the preparation of compound libraries of Michael acceptors with tunable reactivity toward nuclophilic selenocysteine residue of thioredoxin reductase, a range of 3-arylglutaconic acids were required. The existing methods at the time had limited scope or involved several steps. A hitherto undescribed protocol for direct palladium(II) acetate-catalyzed arylation of glutaconic acid dimethyl ester at position 3 has been developed with a diverse set of arenediazonium tosylates followed by hydrolysis. This generally good-yielding two-step sequence displayed a propensity to deliver E -configured coupling products while compounds mostly featured in the literature were predominantly Z -configured. The possibility for preparing a library of 4-arylpyridine-2,6(1 H,3 H)-diones has been exemplified.

Atslēgas vārdi
arylpent-2-enedioic acids, diazonium tosylate, ester hydrolysis, glutaconic acid, imide synthesis, Pd-catalyzed coupling, regiospecificity
DOI
10.1055/s-0037-1611211
Hipersaite
https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0037-1611211

Dar`in, D., Kantin, G., Žalubovskis, R., Krasavin, M. Flexible Entry into 3-Arylpent-2-enedioic Acids via Heck-Matsuda Arylation of Dimethyl Glutaconate with Arenediazonium Tosylates. Synthesis, 2019, Vol. 51, No. 10, 2230.-2236.lpp. ISSN 0039-7881. Pieejams: doi:10.1055/s-0037-1611211

Publikācijas valoda
English (en)